Study Of Flavonoids From Lycopus Lucidus Turcz.ex Benth

Plants of the Lycopus L. (Lamiaceae) genus are rich sources of flavonoids, coumarins, terpenoids, and tanning agents. Many of them are used in folk and scientific medicine.The aerial part of Lycopus lucidus Turcz.ex Benth.(shiny lycopus) is used in folk medicine as a tonic, cardiotonic, and wound-healing and pain relieving agent.Ground air-dried raw material collected during flowering (June 1999) on the northeast slope of the Tien Shan mountains (Xinjiang region, P. R. China) was extracted with ethanol at room temperature.The combined alcohol extract was evaporated in vacuum. The condensed solution was diluted with water and successively treated with petroleum ether, ethylacetate, and butanol. The solvents were removed to afford petholeum-ether, ethlacetate, butanol fractions, water fraction.The ethylacetate fraction was chromatographed over a silica-gel column with gradient elution by CHCI3-CH3OH (98:2-85:15) to afford 1-5. These compounds were identified using UV, MS and NMR spectra, chemnical transformations, HPLC and comparison with authentic samples.Compound L-1: Chrysoeriol (5,7,4'-trihydroxy-3'-methoxyflavone), C16H12O6 (M+ 300), mp 336-337℃ (dec.).Compound L-2: Luteolin (5,7,3',4'-tetrahydroxyflavone), C15H10O6 (M+ 286), mp 329-331℃ (dec.)Compound L-3: Quercetin (3,5,7,3', 4'-pentahydroxyfl,avone), C15H10O7 (M+ 302),mp312-314℃.Compound L-4: Cinaroside (luteolin-7-O-β -D-glucoside), C21H20O11 (M+ 448), mp 240-242℃.Compound L-5: Quercimeritrin (quercetin-7-O- β -D-glucoside), C21H20O12 (M+ 464),mp249-250℃.The butanol fraction was chromatographed over a silica-gel column with gradient elution by CHCI3-CH3OH (95 : 5 - 80 : 20) to afford 6-9. These compounds were identified using UV, MS, and NMR spectra, chemical transformations, HPLC and comparison with authentic samples.Compound L-6: Chrysoeriol-7-O- β -D-glucoside, C22H22O11 (M+ 462), mp 173-175℃(dec.)Compound L-7: Miquelianin (quercetin-3-O- β -D- glucoside), C21H20O12 (M+ 464), mp 236-23 8℃.Compound L-8: Rutin C27H30O16(M+ 610), mp 193-195℃.Compound L-9: Isorhamnetin-3-O-β -D-glucoside-(6→1)-L-rhamnoside.Flavonoids from L-l to L-9 are isolated for the first time from L.lucidus.